(R)-1-Arylethanols from aryl iodides through a two-step one-pot enantioselective chemoenzymatic process

Journal of Molecular Catalysis B: Enzymatic

Volumn 61, Issue 3-4, 2009, Pages 184-187

  Cacchi, Sandro ^a   Cirilli, Roberto ^b   Fabrizi, Giancarlo ^a   Sgalla, Simona ^b   Macone, Alberto ^a   Bonamore, Alessandra ^a   Boffi, Alberto ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b ISTITUTO SUPERIORE DI SANITÀ   (Italy)

Author keywords

Alcohol dehydrogenase; Asimmetric synthesis; Palladium catalysis

Indexed keywords

ACETIC ANHYDRIDES; ACETOPHENONES; ALCOHOL DEHYDROGENASE; ARYL IODIDES; ENANTIOSELECTIVE; ENANTIOSELECTIVE REDUCTION; LACTOBACILLUS BREVIS; ONE POT; ONE POT PROCESS; PALLADIUM CATALYSIS; PALLADIUM-CATALYZED CONVERSION;

CATALYSIS; ENZYMES; KETONES;

PALLADIUM;

1 ARYLETHANOL; ACETIC ANHYDRIDE; ACETOPHENONE DERIVATIVE; ALCOHOL; ALCOHOL DEHYDROGENASE; PALLADIUM; UNCLASSIFIED DRUG;

ALCOHOL METABOLISM; ALCOHOL PRODUCTION; ARTICLE; CHIRALITY; CONTROLLED STUDY; ENANTIOSELECTIVITY; ENZYME MECHANISM; LACTOBACILLUS BREVIS; NONHUMAN; REDUCTION KINETICS;

LACTOBACILLUS BREVIS;

EID: 72049130562     PISSN: 13811177     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcatb.2009.06.009     Document Type: Article

References (30)

1. Ali A., Thompson C.F., Balkovec J.M., Graham D.W., Hammond M.L., Quraishi N., Tata J.R., Einstein M., Ge L., Harris G., Kelly T.M., Mazur P., Pandit S., Santoro J., Sitlani A., Wang C., Williamson J., Miller D.K., Thompson C.M., Zaller D.M., Forrest M.J., Carballo-Jane E., and Silvi L. J. Med. Chem. 47 (2004) 2441-2452
2. Wu H., Smith T.A., Huang H., Wang J.B., Deschamps J.R., and Coop A. Bioorg. Med. Chem. Lett. 17 (2007) 4829-4831
3. Bichlmaier I., Kurkela M., Joshi T., Siiskonen A., Tobias Rüffer T., Lang H., Finel M., and Yli-Kauhaluoma J. ChemMedChem 2 (2007) 881-889
4. Thiel O.R., Bernard C., King T., Dilmeghani-Seran M., Bostick T., Larsen R.D., and Faul M.M. J. Org. Chem. 73 (2008) 3508-3515
5. Thurmond J., Butchbach M.E.R., Palomo M., Pease B., Rao M., Bedell L., Keyvan M., Pai G., Mishra R., Haraldsson M., Andresson T., Bragason G., Thosteinsdottir M., Bjornsson J.M., Coovert D.D., Burghes A.H.M., Gurney M.E., and Singh J. J. Med. Chem. 51 (2008) 449-469
6. Suri J.T., Vu T., Hernandez A., Congdon J., and Singaram B. Tetrahedron Lett. 43 (2002) 3649-3652
7. Zhou Z., and Guo Y. Synth. Commun. 38 (2008) 684-696
8. Hadzovic A., Song D., MacLaughlin C.M., and Morris R.H. Organometallics 26 (2007) 5987-5999
9. Cheung F.K., Lin C., Minissi F., Crivillé A.L., Graham M.A., Fox D.J., and Wills M. Org. Lett. 9 (2007) 4659-4662
10. Chai L., -T-, Wang W.W., Quan-Rui Wang Q.-R., and Tao F.-G. J. Mol. Catal. A: Chem. 270 (2007) 83-88
11. Baratta W., Chelucci G., Herdtweck E., Magnolia S., Siega K., and Rigo P. Angew. Chem. Int. Ed. 46 (2007) 7651-7654
12. Le Roux E., Malacea R., Manoury E., Poli R., Gonsalvi L., and Peruzzini M. Adv. Synth. Catal. 349 (2007) 309-313
13. Cheemala M.N., Gayral M., Brown J.M., Rossen K., and Knochel P. Synthesis (2007) 3877-3885
14. Ahlford K., Zaitsev A.B., Ekström J., and Adolfsson H. Synlett (2007) 2541-2544
15. Paredes P., Diez J., and Gamasa M.P. Organometallics 27 (2008) 2597-2607
16. Alza E., Bastero A., Jansata S., and Pericàs M.A. Tetrahedron: Asymmetry 19 (2008) 374-378
17. Liu G., Yao M., Zhang F., Gao Y., and Li H. Chem. Commun. (2008) 347-349
18. Sui-Seng C., Freutel F., Lough A.J., and Morris R.H. Angew. Chem. Int. Ed. 47 (2008) 940-943
19. Gröger H., Rollmann C., Chamouleau F., Sebastien I., May O., Wienand W., and Drauz K. Adv. Synth. Catal. 349 (2007) 709-712
20. Kurbanoglu E.B., Zilbeyaz K., Kurbanoglu N.I., and Kilic H. Tetrahedron: Asymmetry 18 (2007) 2332-2335
21. Martín-Matute B., Edin M., Bogár K., Kaynak F.B., and Bäckvall J.-E. J. Am. Chem. Soc. 127 (2005) 8817-8825
22. Martín-Matute B., and Bäckvall J.-E. Curr. Opin. Chem. Biol. 11 (2007) 226-232
23. Cacchi S., Fabrizi G., Gavazza F., and Goggiamani A. Org. Lett. 5 (2003) 289-291
24. Müller M., Wolberg M., Schuber T., and Hummel W. Adv. Biochem. Eng. Biotechnol. 92 (2005) 261-287
25. Niefind K., Müller J., Riebel B., Hummel W., and Schomburg D. J. Mol. Biol. 327 (2003) 317-328
26. In: Gladysz J.A., Curran D.P., and Horvath I.T. (Eds). Handbook of Fluorous Chemistry (2004), Wiley-VCH, Weinheim
27. Kirsch P. Modern Fluoroorganic Chemistry. Synthesis Reactivity, Applications (2004), Wiley-VCH, Weinheim
28. For a recent biocatalytic synthesis of optically active (R)-4-fluorophenylethan-1-ol from 4-fluoroacetophenone, see reference 5b.
29. Wan Y., Alterman M., Larhed M., and Hallberg A. J. Org. Chem. 67 (2002) 6232-6235 (For the utilization of DMF as carbon monoxide source)
30. Verbit L. J. Am. Chem. Soc. 87 (1965) 1617-1619